3,4,6,10b-tetrahydro-1H-[1,4]-oxazino[3,4-a]isoindole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3,4,6,10b-tetrahydro-1H-[1,4]-oxazino[3,4-a]isoindole
• 英文别名: 3,4,6,10b-tetrahydro-1H-[1,4]oxazino[3,4-a]isoindole
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: FXGXAVKJZHCZHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(苯基甲基)吗啉 在 双氧水 、 乙酸酐 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 3,4,6,10b-tetrahydro-1H-[1,4]-oxazino[3,4-a]isoindole
  参考文献：
  名称：

  On the non-classical course of Polonowski reactions of N-benzylmorpholine-N-oxide (NBnMO)

  摘要：

  The Polonowski reaction of NBnMO (4) afforded tropone (10) and the novel isoindole 11 besides the expected products benzaldehyde and acetmorpholide, in a temperature-dependent ratio. The reaction proceeded via two primary carbenium-iminium ion intermediates, an exo-centered species 5 which underwent a benzylium-tropylium type rearrangement, and a ring-centered species 6, which reacted further to isoindole 11 by intramolecular electrophilic substitution. The experimental findings were in good agreement with DFT computational data. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.001

文献信息

• On the non-classical course of Polonowski reactions of N-benzylmorpholine-N-oxide (NBnMO)
  作者：Thomas Rosenau、Peter Schmid、Paul Kosma

  DOI：10.1016/j.tet.2005.02.001

  日期：2005.4

  The Polonowski reaction of NBnMO (4) afforded tropone (10) and the novel isoindole 11 besides the expected products benzaldehyde and acetmorpholide, in a temperature-dependent ratio. The reaction proceeded via two primary carbenium-iminium ion intermediates, an exo-centered species 5 which underwent a benzylium-tropylium type rearrangement, and a ring-centered species 6, which reacted further to isoindole 11 by intramolecular electrophilic substitution. The experimental findings were in good agreement with DFT computational data. (c) 2005 Elsevier Ltd. All rights reserved.